Yarn treating processes and compositions therefor



Patented July 11, 1939 PATENT OFFICE YARN TREATING PROCESSES AND COMPO-SITIONS THEREFOR Joseph B. Dickey and James B.

Rochester, N. Y., aaslgnors Comp y, Rochester, N. Y.,

New Jersey Normington. to Eastman Kodak a corporation of No Drawing.Application November 26, 1937, Serial No. 176,698

18Glaims.

This invention relates to the conditioning of textile yarns and moreparticularly to the conditioning of filaments and yarns composed oforganic derivatives of cellulose such as cellulose acetate, celluloseacetate propionate, cellulose acetate butyrate, etc., to render themmore amenable to textile operations such as knitting and the like.

As is well-known in the manufacture of yarns, particularly thosecomposed of or containing cellulose organic derivatives, it is necessaryto treat the yarn in order to reduce the tendency toward breakage of theindividual filaments or fibers when they are subjected to variousmechanical strains and to lubricate the yarn in order to fa cilitatehandling in such operations as spinning, twisting, winding and reeling.In addition, it is necessary to treat the yarn'to adapt it for. use

' erations.

as warp or filling. or for thernanufacture ofvarions-types oflmittedfabrics. In knitting, it is particularly important that the yarn be-softand pliable in order that it may conform readily to the contour oftheneedles and thus produce a closely knit fabric free from such defects asstitch distortion, "pin holes," ladderin and the like.

Eeretofore it hasbeen proposed to employ softening agents such aspolyhydric" alcohols andsimllar agents as ingredients of yarnconditioning or lubricating formulas, generally in connectlon withmineral, animal or vegetable oils. It has been found, however, that mostof the known softening agents and the variousformulae containingthemhave certain drawbacks, one of the mostserlous of which is high vaporpressure, and'in some cases too drastic a solvent action on the yarn.Many of such agents possess slight or insufiicient solvent power for thelubricants with which they are used and it is accordingly necessary toemploy blending agents or emulsifying agents in order to obtain operableyarn treating formulae. In addition, many of the known softening andlubricating agents are insufficiently soluble in water to permitsatisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely newclass of yarn conditioning agents which are particularly adapted for thetreatment of yarns composed of or containing organic derivatives ofcellulose and capable of lubricating, softening and rendering such yarnsmore amenable to knitting and other textile op- A further and specificobject is to provide a class of conditioning agents which augment orassist the lubricating action of various lubricants when applied to suchyarns. A still further object is to provide yarn softening andlubricatlng formulae which can be readily. re-

moved from the by the scour baths.

A still further object is to provide an improved method for theconditioning of yarns, particularly those composed of or containingorganic derivativesoi' cellulose such as cellulose acetate,

whereby the yarn is rendered soft and pliable and capable of employmentin a variety of textile operations where complicated designs or stitchesare employed. Other objects will appear hereinafter.

These objects are accomplished by the follow ing invention which in itsbroader aspects comprises the discovery that acetal esters having thegeneral formula:

groups, may be used as yarn conditioning agents and particularly assoftening agents with or without the addition of animal, mineral orvegetable oils in the treatment of yarns composed of or containingorganic derivatives of cellulose.

We have found that these compounds have a slight solvent and/orsoftening action on cellulose organic derivative yarns which renderssuch yarns soft and pliable without at the same time having too drastica'solvent action thereon.

In accordance with the invention these compounds may be applied directlyto the yarn during or after spinning, or may be added to the spinningsolution itself. I We have found that these compouds have exceptionalsolvent powers which enable them to dissolve mineral oils and blown andunblown, drying and semi-drying, vegetable and animal oils andaccordingly they may be. and preferably are, employed as ingredients ofyarn conditioning or lubricating formulae in conjunction with agentswhich function wholly or partially as lubricants.

In the following examples and description we have set forthseveral ofthe preferred embodi-. ments of our invention.- but they are. includedmerely for purposes of illustration and not as a limitation thereof.

The preparation of the above indicated class of compounds which we havefound especially valuable as yarn conditioning agents may be carried outin known manner. An example of the preparation of a typical compound ofthis class is as follows:

Preparation of tetrahgdrofariural glycerol acc- 'tate.-l mol oftetrahydrofurfural glycerol and Example III: Percent Ethylidine glycerolmethoxy acetate... Blown olive oil 40 Example IV:

Methyl ethyl ketone glycerol propionate- 70 Light mineral oil; 30

Example V; v v Propylidine glycerole lactate 30' Neats-foot oil 70Example VI:

Cyclohexanone glycerol propiona 20 Blown neats-foot oil 80 Sulfonatedolive oil 20 White. mineral oil...'.'.'. 10 Oleic acid 10 Ethanolamin 8Water 7 Example VII: L

Butylioine glycemie ethoxy acetate 20 Sperm o 60 Laura] 30 Example VIIIv Benzylidine glycerol lactate 50 Blown sperm oil 20 Sulfonated castoroil 30 on the steam bath for 7 hours. Fractionation of the solutiongives the ester tetrahydrofurfural glycerol acetate having aboiling'point of 153-6 C. at 14 mm. in an 80% yield.

In an exactly similar manner there may be prepared tetrahydrofurfura'lglycerol propionate boiling at 162-167? C. at 16 mm. andtetrahydrofurfural butyrate boiling at l55-160'C.-at 8 mm.

Our invention will be more readily understood by reference to thefollowing examples in. which typical applications of the invention areset forth:

Example I.-Yarn designed primarily for knit- I ting and composed ofcellulose acetate is treated by applying .theretotetrahydroflrfurylidlne' glycerol acetate. The amount of the conditioning liquidmayrun from 445% 'by weight of the untreated yarn. If the yarn isintended for weaving, the same procedure may be followed except that theamount of conditioning agent added to the yarn is only about l-%.

Example II.--A conditioning liquid is made up by mixing the followingingredients in the indicated proportions:

. Per cent -Glycerol acetone acetate '10 Olive oil 30 This compositionis applied to a cellulose acetate yarn intended for knitting in anamount representing 4-25% by weight of the untreated yarn. The filamentsor fibers treated with this composition are quite soft and pliable andgive excellent results in textile operations, especially knitting.

tions which may be applied to various types of yarns, particularly thosecomposed of or containing cellulose acetate, cellulose acetatepropicnatc. and similar cellulose organic derivative yarns in such yarnssoft and pliable and well-adapted for are the following:

Example IX.--A 20% solution of cellulose acetate in acetone in which isincorporated"1-35% Other examples of yarn-conditioning composi-- mentsthus prepared are pliable and suitable for knitting.

Other examples yarn conditioning agents which may be employed inaccordance with our invention are the following:

Example X: Per cent Water 80 Gelatin 5 Glycerol acetone acetate--- 10Sulfonat'ed olive oil I 5 Emmple XI:

Water a 80 Water soluble cellulose ester 5 Ethylidine glycerol g1ycoiatea 10 Diethylene glycol 5 Example XII: Parts Blown teaseed oil Glycerolacetone propionate '15 25 Example XIII:

Teaseed oil I, 25 Oleic acid 25 Sulfonated castor oil Glycerol acetoneacetate 20 30 Example XIV:

Blown neats foot oil 25 Cetyl sulfate ammonium salt 4 Oleie acid '20Mineral oil I0 Glycerol acetone acetate 25 As will be apparent from theabove examples and description, the conditioning agents of our inventionmay be. applied by! wide variety of 9 methods. For example, we mayemploy the agent as an ingredient of the spinning dope from which thefilaments are formed, the amount of the agent so employed depending upona number of factors, such as the particular cellulose derlvatlve used inmaking the yarn, the solvent or solvent combination used in making upthe spinning solution, and the degree of softness or pliabllity desiredin the yarn, etc.

If the conditioning agent is to be applied to the yarn after spinning,this may be done by bringing the yarn in contact with a wick, roll, orfelt .wet therewith or the liquid may be applied by immersion, spray orotherwise. The particular point at which the liquid is applied may vary.so It may, for example. be applied to the yarn inside or outside thespinning cabinet, between the I guide and godet roll, between the godetor other roll or guide and the point of winding and/or twisting. In,some caseszthe liquid may even be applied-to the yarn after winding ontocones, spools, bobbins, or the like or by the so-called bobbin to bobbinmethod. In the case of staple iiber manufacture the liquid may beapplied to the yarn prior to, or after cutting into staple le xths. v

111e amount of the scent so employed will vary widely depending upon theresults desired, the

by weight,'based on the weight of the dry yarn, u

f the above compositions, we have found that those of Example VI andVII, characterized by the presence therein of cyclohexanone glycerolpropionate and benzylidine glycerol lactate, respectively, and those ofExamples X, XIII and XIV, characterized by the presence thereinofglycerol acetone acetate are unique in their abiiity to reduce oreliminate accumulations of static electricity on yarns of the typeherein referred to, particularly when such yarns are employed for themanufacture of cut staple fibers. It is therefore one of the specificfeatures of our invention to employ these compositions as anti-staticagents generally, and specifically for the manufacture of cut stapleyarns. In producing cut staple fibers, the selected composition may bedeposited on the fiber after the cutting operation in any convenientmanner, as by a conventional type of applicator, by spray, immersion orthe like. Cut staple fibers treated in this manner display a very markedreduction in their tendency to accumulate charges of static electricityand in many cases this tendency is substantially or completelyeliminated. I

Although in the above examples we have referred primarily to yarntreating compositions containing. only the conditioning agent and an;

oil, other ingredients such as solvents, non-solvents, emulsifyingagents, blending agents and the like, may be added within the scope ofour invention. Likewise, various dyes or other. coloring. matter may beincluded in case it is desiredto permanently or fugitively tint or dyethe material undergoing treatment. I

Although we have found it convenient to illustrate our invention byreference to compositions containing specific percentages of the variousingredients, these percentages may vary widely depending upon theparticular purpose for which the composition is intended. For example,if it is desired to control'the solvent or softening action of theconditioning agent, the amount of the agent may be adjusted as, forexample, by reducing the amount of the agent and correspondinglyincreasing the amount of oil or other ingredient.

While we .have described our invention with.

particular reference -to the treatment of yarns composed of organicderivatives of cellulose such as cellulose acetate, the conditioningagents and formulaedesc'ribed herein are applicable to the condition ofmany other types of cellulose derivative yarns such as those "composedof or containing cellulose propionate, cellulose butyrate,celluloseacetate propionate, cellulose acetate butyrate, ethylcellulose, methyl cellulose, benzyl cellulose and others, as well as tothe condition 'ing of silk, wool, cotton, viscose and other natural orartificial materials.

The term yarn as used herein and in the claims is to be understood asincluding a single filament, a plurality of filaments associated ..into

the form of a thread, either of high or low twist,

single or multiple threads associated or twisted together, compositethreads composed of a mixture of natural and artificial filaments or acomposite thread formed by twisting together individual strands ofnatural or artificial materials, as well as cut staple fibers producedfrom natural and/or artificial filaments or threads and spun yarnproduced from such staple fibers.

- As indicated above, the yarn conditioning up a variety of yarntreating formulae of varying composition.

The yarn conditioning method and compositions of our invention possessmany outstanding advantages. characteristic of the agents employed inaccordance with the invention is their ability to soften yarns,especially those composed ofor contain-- ing organic derivatives ofcellulose such as cellulose acetate and render them soft and pliable andamenable to various textile operations, especially operations such asthose involved in weaving and knitting where complicated designs orstitches are employed, without too drastic an action on the yarnmaterial. Another outstanding characteristic of thesecompounds is theirexceptional solvent power for a wide variety of mineral, animal andvegetable oils and their ability-to act as lubricating assistants inconjunction with these oils when applied to such yarns. In addition, dueto their solubility in water, they may be readily removed from yarns andfabrics by means of the usual aqueous scour baths. By employing the'yarnconditioning agents and method of our invention as herein described, oneis enabled to '3 obtain highly satisfactory results in the manufacture.of yarns and woven fabrics. and especially the production from theseyarns of closely knit fabrics free from defects such as pin holes,stitch distortion, laddering and the like.

What weclairn and desire to secure by Letters Patent of the UnitedStates is:

1. The process of conditioning yarn to render it more amenable totextile operations including knitting, weaving, spinning and the likewhich comprises applying thereto a lubricating and softening compositioncontaining as its essential sisting of hydrogen, part of a cyclic chainof carbon 'atoms, alkyl, aryl, and heterocyclic groups; and wherein in Ra substituent of the group consisting of hydrox'y and a'lkoxy groups mayreplace hydrogen. Y

'2. The process of conditioning yarn composed of or containing organicderivatives of cellulose to render it more amenable to textileoperations including knitting, weaving, spinning and the like whichcomprises applying thereto a lubricating and softening compositioncontaining as its essential lubricating and softeningcompound 'acetalesters having the formula:

The fundamental and outstanding are substituents selected from the groupconsisting of hydrogen, part of a cyclic chain of carbon atoms, alkyl,aryl, and heterocycllc groups; and wherein in R a substituent of thegroup consisting of hydroxy and alkoxy groups may replace hydrogen.

- 3. The process 01! conditioning yarn composed or or containingcellulose acetate to render it more amenable to-textile operationsincluding knitting, weaving, spinning and the like, which comprisesapplying thereto a lubricating and softening composition containing asits essential lubricating and soitening component an acetal ester havingthe "formula:

4. The process of conditioning yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning and the like, which.

comprises applying thereto a lubricating and softening compositioncontaining as its essential lubricating and softening component acetalesters having the formula:

7 I where R is a substituent selected from the group consisting ofhydrogen and alkyl; R and R'fiare substituents selected from the groupconsisting of hydrogen, part of a cyclic chain of carbon atoms, alkyl,aryl, and heterocyclic groups; and wherein in R a substituent of thegroup consisting of hydroxy and alkoxy groups may replace hydrogen.

5. The process of conditioning yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning and the like, which comprises applyingthereto a. lubricating and softening composition containing as itsessential lubricating and softening component glycerol acetone acetate.

6. The process of conditioning yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning and the like, which comprises applyingthereto a lubricating and softening composition containing as itsessential lubricating and softening component ethylidine glycerolmethoxy acetate.

7. The process of conditioning. yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning and the like, which comprises applyingthereto a lubricating and softening composition containing as itsessential lubricating and softening component methyl ethyl ketoneglycerol pr'opionate.

8. A conditioning agent for rendering yarns more amenable to textileoperations including knitting, weaving,. spinning and the like whichcomprises acetal esters having the formula:

7 RI! R! where R is a substituent selected from the group consisting ofhydrogen and aikyl; R. and R" are substituents selected from the groupconsisting of hydrogempart ot a cyclic chain oi carbon, atoms. alkyl,aryl, and heterocyclic groups; and wherein in R a substituent oi thegroup consisting 0! hydroxy and alkoxy groups may replace hydro- 9. Aconditioning agent for rendering textile yarns composed of or containingorganic derivatives of cellulose more amenable to textile operationsincluding knitting, weaving,-spinning and the like which comprisesacetal esters having the formula:

RI! n! where R is a substituent selected from the group consisting ofhydrogen and alkyl: R and Rf are substituents selected from the groupconsisting of hydrogen, part of a cyclic chain of carbon atoms, alkyl,aryl, and heterocyclic groups; and wherein in R a substituent oi thegroup consisting of hydroxy and alkoxy groups may replace hydro gen.

10. A conditioning agent for rendering yarns composed of or containingcellulose acetate more amenable to textile operations includingknitting, weaving, spinning and the like containing glycerol acetoneacetate.

11. A conditioning agent for rendering tentile yarns composed of orcontaining cellulose acetate more amenable to textile operationsincluding knitting, weaving, spinning and the like containlng ethylidineglycerol methoxy acetate;

12. A conditioning agent for rendering textile yarns composed of orcontaining cellulose acetate more amenable to textile operationsincluding knitting, weaving, spinning and the like containing methylethyl ketone glycerol propionate.

13. Textile yarn amenable to textile operations including knitting,weaving, spinning and the like impregnated with a lubricant containingacetal esters having the formula:

' consisting of hydrogen and alkyl; R and R are suhstituents selectedfrom the group consisting of hydrogen, part of a cyclic chain of carbonatoms, alkyl, aryl, and heterocyclic groups; and wherein in R asubstituent of the group consisting of hydroxy and alkoxy groups mayreplace hydrogen.

14. Textile yarn composed of or containingpb ganic derivatives 01'cellulose amenable to textile operations including knitting, weaving,spinning and the like, impregnated with a conditioning I where R is asubstituentselected from the group consisting of hydrogen and alkyl; Rand R." are substituents selected from the group consisting of hydrogen,part-of a cyclic chain of carbon atoms, alkyl, aryl, and heterocyclicgroups; and. wherein in R a substituent of the groupconsisting of fililhydroxy and aikoxy groups may gen.

15. Textile yarn composed of or containing organic derivatives ofcellulose amenable to textile operations including knitting, weaving,spinning and the like, impregnated with a conditioning agent comprisingacetal esters having the formula:

replace hydroincluding knitting, weaving,

like, impregnated with a lubricant comprising where R is a substituentselected from the group consisting 0% hydrogen andalkyl; R. and R', aresubstituents selected from the group consisting vo! hydrogen, part of acyclic chain of carbon atoms,

' alkyl, aryl, and heterocyclic groups; and wherein in R a substituentof the group consisting of hydroxy and alkoxy groups may replacehydrogen.

16. Textile yarns composed of or containing cellulose acetate amenableto textile operations including knitting, weaving, spinning and thelike, impregnated with a lubricant comprising glycerol acetone acetate.

1'1. Textile yarns composed of or'containing cellulose acetate amenableto textile operations including knitting, weaving, spinning and thelike, impregnated with a lubricant comprising ethylidine glycerolmethoxy acetate.

.18. Textile yarns composed of or containing cellulose acetate amenableto textile operations spinning and the methyl ethyl ketone glycerolpropionate.

JOSEPH B. DICKEY. JAMES B. NORNIINGTON.

